Check in on the 2021 developing calendar of events in
Key West and The Florida Keys.
Please be aware that due to covid events may be cancelled or rescheduled.
APRIL
April 1 – April 29
The Studios of Key West presents: April Exhibitions
Four exhibitions fill the Studios’ galleries this month. Discover the creative works of Olga Manosalvas, known for her colorful paintings and sculptures; Former Artist in Residence and watercolor artist, Scott Ponemone; photographer Kyla Piscopink; and local author Rita Troxel. View galleries in person or online. Galleries open Tue-Sat., 12-4 p.m., free.
April 27 – May 1
Mile 0 Fest
Mile 0 Fest is 5 Day Red Dirt/Americana Music Festival in Paradise (aka Key West).
Mile 0 Fest was founded in 2017, with it’s first year of production being 2018. It was created on the principle of producing a festival that checked all of the boxes:
- Fantastic Line-Up – that has repeat and fan favorites back every year, but also brings in new faces, and fresh talent. The best in Red Dirt Americana
- Location, Location, Location – A destination that was enjoyable for everyone! Key West has everything, beaches, fishing, water-sports, history, shopping, dining, dancing, it’s the perfect vacation.
- Fan Bliss – A festival that puts the fans first. No overcrowding here, we are a boutique festival with an attendance cap. Over a short period of time, our attendees have become family. With almost every state represented, music fans from all over the country come together once a year to celebrate the common thread that binds them. The Love of great music.
It is held annually in January, with the dates announced late spring the year before and the line-up announced July 4th every year. UPDATE: Due to Covid 19 – Mile 0 Fest 2021 will be held April 27th-May 1st, 2021
Mile 0 Fest is held in Key West, Florida. We utilize numerous stages all over the island with our biggest stage being the Truman Waterfront Park Amphitheater. Local venues like The Smokin’ Tuna, Irish Kevin’s, Durty Harry’s, Viva Saloon, The Southernmost Beach Resort & Cafe, The Southernmost House, Sunset Pier, Cowboy Bill’s, Key West Theater, The San Carlos Institute, Fury Cruises, and many more are also utilized throughout the week to provide ample opportunity to check out Key West while enjoying your favorite Red Dirt/Americana Artists.
April 30
Arbor Day at Key West Tropical Forest & Botanical Garden
The Garden is offering free admission all day. The Garden’s plant Nursery will be open for plant sales from 9am to Noon and will offer a 50% discount on Crabwood, Coffee colubrina and Princewood trees. A ceremonial “Arbor Day” tree planting will take place at 1pm. Guided Docent tours will be offered at 10:30am and 1pm. Groups will be limited to 10 people and masks will be required. Registration for the tours can be made in advance
December 1 – July 31
Key West Fishing Tournament
Anglers of all ages and abilities can target more than 40 species of fish in the Key West Fishing Tournament, a free-entry multidivision challenge that takes place Dec. 1, 2020, to July 31, 2021.
Now in its 55th year, the tournament features divisions for men, women, junior anglers ages 10 to 15 and Pee Wees under 10 years old — making it ideal for families that want to share the angling experience.
MAY
April 27 – May 1
Fourth Annual Mile 0 Fest Key West
This annual fest brings the best of Americana and Red Dirt Music to the island paradise for five full days of bands, acoustic jams and songwriter swaps. Event organizers are to have safety protocols in place per COVID-19 guidelines.
Apr 21 – Dec 31
History of Diving Museum Exhibit: Diving in Pop Culture
Visit the museum at 82990 Overseas Highway (mile marker 83) to see the latest exhibit with representations of diving in literature, advertising, film, television, games, music, attractions, collectibles, and more, while examining connections amongst these works. Museum staff has been collecting and researching all of the creative ways diving has been incorporated into pop culture for over 100 years.
Apr 22 – May 15
Marathon Community Theater presents: Suite Surrender
Marathon Community Theater, located at 5101 Overseas Highway, presents the comedic farce by Michael McKeever. It’s 1942, and two of Hollywood’s biggest divas have descended upon the luxurious Palm Beach Royale Hotel — assistants, luggage, and legendary feud with one another in tow. Everything seems to be in order for their wartime performance…that is, until they are somehow assigned to the same suite. Mistaken identities, overblown egos, double entendres, and a lap dog named Mr. Boodles round out this hilarious riot of a love note to the classic farces of the 30s and 40s. And who doesn’t need hilarious right now?!
May 4 – May 18
Connections Project Mural: A Mosaic of the Keys
The Connections Project mural, titled “A Mosaic of the Keys” is made up of individual 6-by-6-inch canvases that were decorated by local artists and creative residents, with the completed pieces arranged into the colorful mosaic. Art lovers can see the mural during a Keyswide “road show” tour, culminating May 4-18 at Key West’s Royal Furniture.
May 5 – May 9
Key West Songwriters Fesitival
Since 1997, BMI has been a presenting sponsor of the festival, the largest festival of its kind in the world, and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.
May 7, 2021 – May 8
15th Annual Mother’s Day Dolphin Tournament
Fish For A Cause! Join a fun and festive one-day fishing tournament for the heaviest Mahi-Mahi. The entire event is a fundraiser to help Habitat for Humanity of the Middle Keys build 11 more affordable homes in Marathon, starting in 2021. This angler tournament awards four categories: Professional, Weekend Warrior, Ladies Only and Jr. Angler (age 16 cutoff).
May 22
Pride Follies
Pride Follies returns to headline this year’s PRIDE celebration presented by the Key West Business Guild. Fantasy Fest Queen Destiny Montgomery is to direct this year’s presentation of Key West talent not usually seen on a professional stage, at the Key West Theater, 512 Eaton St.
May 23
Rams Head presents: Sammy Hagar & The Circle at coffee Butler Amphitheater
Key West announces Sammy Hagar & The Circle, one of rock music’s most dynamic supergroups! Tickets will go on sale Friday, April 9 at 12PM (ET) online as well as the Key West Theater’s Box Office located at 512 Eaton St. Doors open 5:30 p.m., show starts 7 p.m. Enjoy an evening with plenty of food vendors, bars, take home items from local artisans and a one-in-a-million view of the Gulf of Mexico.
May 27
Key West Whiskey Fest
This inaugural food, drink, and music festival is one of the most eagerly awaited on Florida Keys’ busy social calendar. Featuring top-class whiskey, Popular highlights will include a range of Tastings, Whiskey walks, Workshops, Brunches, and plenty more.
May 28
Rams Head presents: Ana Popovic
Enjoy an evening with this acclaimed blues rock artist who is referred to as ‘one helluva guitar player.’ Tickets on sale starting April 14 at noon. Performance at Key West Theater.
May 29
2nd Annual Key West Blues Festival.
This is all I could find on this yet.
May 29 – May 30
Afro Roots Fest Islamorada
Afro Roots World Music is one of the longest-running events of its kind. The festival started at Tobacco Road, and has been staged at various locations throughout South Florida. Afro Roots, now regional, spans from Jupiter to Key West. May 29, starting at 6 p.m. at Florida Keys Brewing Co., enjoy the musical sounds of Electric Piquete, a two-time award-winning Latin funk outfit, and JUKE, a four-piece, ‘post-blues’ hybrid with a high motor and bottomless soul. May 30 entertainment includes the Miami-based power quartet, Electric Kif, and Miami’s Afro Galactic / Tropidelic funksters, Nag Champayons.
JUNE
June 1 – June 2
Rams Head presents: the Allan Betts Band with Special Guests, The River Kittens
After a successful tour as The Devon Allman Project with special guest Duane Betts, the sons of Gregg Allman and Dickey Betts have joined forces to form The Allman Betts Band. Each evening of live music features new songs from their solo projects and classic Allman Brothers and Gregg Allman tunes. Tickets on sale starting April 14 at noon. Performances at Key West Theater
June 2 – 6
Key West Pride
Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, and pageants to select Mr., Miss and Ms. Key West Pride.
June 4
Seventh annual Skippers Dolphin Tournament
This tournament is headquartered at Skippers Dockside Restaurant behind Key Largo’s Holiday Inn. Cash prizes of over $60,000 include a first-place prize of $20,000 as well as prizes for the top six teams and top lady and junior anglers.
June 4 – June 6
28th annual Original Big Pine and Lower Keys Dolphin Tournament
The Lower Keys Chamber of Commerce presents this annual event where anglers contend for over $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds. Additional prizes await winners in open, ladies and youth divisions.
June 5 – June 6
Coralpalooza 2021
Presented by the Coral Restoration Foundation, Coralpalooza is slated as the world’s largest coral restoration event! On World Oceans Day, join a celebration among ocean lovers to actively restore the planet’s third-largest barrier reef. Coralpalooza demonstrates the power of large scale, collaborative acton to save coral reefs. This year’s format, whether it is to be all digital, in-person or a hybrid of the two, is yet to be announced. Check online for updates.
June 7 – June 13
REEF presents: Fish Out of Water Virtual 5k Race
The Key Largo-based Reef Environmental Education Foundation (REEF) is encouraging ocean enthusiasts everywhere to get moving in the name of conservation. Choose to run, walk, hike, bike or even swim, completing the 5K (3.1 miles) in one day or throughout the week. No matter how you participate, it’s a great way to get active in your community while making your miles count. Register before April 30, 2021 for the early bird discounted rate. Registration will remain open through May 28, 2021. All racers will receive a limited-edition race T-shirt, 2021 finishers medal, and bib. Premium registration levels also include a retro fanny pack and two custom vinyl stickers.
June 11 – June 12
Eighth Annual Ladies Dolphin Tournament
Hosted by the Florida Keys Elks Lodge, this event welcomes female angler teams to compete for the highest aggregate weight of three dolphin fish. Cash and prizes are awarded to first- through third-place finishers, and for the largest dolphin caught.
June 11 – June 13
Ladies Let’s Go Fishing Screamin’ Reels Tournament
Intended for novice anglers, this weekend is about learning and a non-intimidating, fun competition with the Ladies Let’s Go Fishing university organizers. Species include legal inshore and offshore fish. Charter a professional boat or fish on your own boat. This is a casual tournament with prizes for heaviest offshore fish, longest inshore fish and drawings for prizes of those who caught fish, plus bonus drawings. Dates and schedule subject to change.
June 12
Swim Around Key West
The Annual Swim Around Key West is a 12.5-mile endurance swim clockwise around the entire island of Key West, started by founder Anna Fugina in 1977. The Annual Swim Around Key West is an independent and insured swim, permitted by the U.S. Coast Guard. There are three categories: solo swimmer, two-person relay team, and three-person relay team. Presented by Key West Athletics Association.
June 16 – June 20
I Love Stock Island Festival
This five day festival is to feature one of a kind Stock Island inspired activities and authentic immersive experience in local community, culture, and art. It’s a great way to celebrate Father’s Day weekend with friends and family in the laidback atmosphere of Stock Island, just across the Cow Key Channel Bridge from Key West.
June 18
Rams Head presents: Past II Present, A Toto Tribute Band
Enjoy an evening of this optimum tribute band performing the music of Toto as well as music that members of Toto have written for other artists. Tickets on sale starting April 14 at noon. Performance at Key West Theater.
June 18 – June 20
VFW Fishing Tournament
A family fun tournament, this event awards up to $3,000 for the heaviest dolphin. All proceeds benefit disabled and needy veterans in Monroe County. A new First Responder category has been added, for Police, Fire Fighters and Paramedics / EMTs to go along with other angler categories.
June 23 – June 24
IFC Captains cup Dolphin Tournament
Teams of up to 4 anglers compete for top prizes, and the total combined weight of 3 fish determines the winning team. If up to 25 boats register, 1st prize cash winnings can reach $25,000.
June 23 – June 27
Mango Fest Key West
Experience all things Mango through shopping, education and demonstrations. Stroll virtually through a vendor village, enter a poetry contest, photo contest, see virtual culinary and cocktail demos and more. Details to come for this 2021 event. Yummm Mangos!!
JULY
December 1 – July 31
Key West Fishing Tournament
More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.
July 1 – July 5
Key Lime Festival
Enjoy a full 4 days of culinary events for every taste, including favorites from past years such as the Key Lime Cocktail Sip & Stroll and Key Lime Pie Hop and new favorites for Key Lime lovers like a Key Lime Scavenger Hunt and Key Lime University! Organizers have also added a few intimate culinary events for VIP Key Lime lovers!
July 10
37th Annual Underwater Music Festival
This annual event for both divers and snorkelers is staged at Looe Key Reef, an area of the Florida Keys National Marine Sanctuary about 6 miles south of Big Pine Key. Hosted by the Lower Keys Chamber of Commerce and a local radio station, US1 104.1 FM, the ocean celebration encourages environmentally responsible diving and preservation of the world’s coral reefs. While the festival’s primary purpose is to promote reef protection and eco-conscious diving, it also offers a bucket-list underwater experience. Some participants might even spot “mermaids” and other costumed characters swaying beneath the waves, adding visual excitement to the unique conservation concert.
July 17 – July 18
Inaugural Florida Keys Brew-BQ
Located at Marathon Community Park the event is expected to feature mouth watering BBQ, and tons of delicious craft beers to wash it down. Highlights also are to include an amateur BBQ cooking competition with prizes, vendors, boats, live music, kids games and more. Daily hours TBD. Sponsored by the Marathon Chamber of Commerce
July 18 – July 21
Del Brown Permit Tournament
Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.
July 21 – July 24
Stock Island Marina Village Key West Marlin Tournament
Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days festival, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total.
July 21 – July 25
Hemingway 5K Sunset Run and Paddleboard Race.
Will update as we get more info
July 22 – July 24
Hemingway Look-Alike Contest
Due to Covid-19, Sloppy Joe’s 40th Hemingway® Contest has been rescheduled for July 22-24, 2021
Whether composing novels in his Whitehead Street writing studio or fishing for big game in local waters, Pulitzer Prize-winning author Ernest Hemingway left a powerful legacy in Key West. His zest for life, literary accomplishments, and enduring affection for the island he called home throughout the 1930s.
AUGUST
August 11 – August 15
Key West Tropical Heat
TROPICAL HEAT is Key West’s HOTTEST event for men! The temperature is not the only thing that will rise during Tropical Heat. The all-male theme parties, pool parties, and adult-oriented entertainment promises to be HOT! August on the Island is always HOT, but during Tropical Heat it promises to be STEAMY! Four days of hot guys and fun, the best way to experience Key West.
August 12 – August 15
25th Annual Key West Lobsterfest
Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. Famous for its sweet and tender meat, the Keys’ spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads.
August 25
Fee-Free Day at Everglades and Dry Tortugas National Parks to Commemorate National Parks Birthday
Celebrate the National Park Service’s 105th birthday! National parks across the country will be hosting in-park programs and virtual experiences. Entrance fees are waived. Everglades National Park normally charges $30.00 per vehicle or vessel, $25.00 per motorcycle, and $15.00 per person for pedestrians, cyclists, and paddle-craft, for a 7-day pass. Dry Tortugas National Park normally charges $15.00 per person over the age of 16, which is good for 7 days. Fees are ordinarily included in the ticket prices for ferry and seaplane tours, but they will not be included on fee-free days.
SEPTEMBER
September 1 – September 5
Key West WomenFest
Just before the school year starts in earnest – just as the last rays of summertime finally set. Just before the holiday season begins to rev up Key West welcomes women from across the globe to an annual celebration that has become one of the largest gatherings of lesbians and friends in North Americas Womenfest! Each year thousands of ladies come together over the Labor Day weekend and stay for a wide range of activities and events during four days of revelry and fun. Key West boasts restaurants that offer remarkable cuisine year-round, watering holes that offer authentic, tropical libations, and shops that can’t be found anywhere else. Of course, the most popular activity during Womenfest usually involves a chaise lounge, a good book, sunscreen, and a killer margarita. Come join us on our little island that is close to perfect but far from normal for this fabulous event that gets bigger and better every year!
September 2 – 6
12th Annual Key West Brewfest
This annual event takes place over Labor Day Weekend and features nearly 200 beers. Join in the fun with beer paired dinners, beer brunches, happy hour parties, pool parties, late-night parties, and of course the Signature Tasting event. VIP tickets grant early admission and other benefits.
Apr 21 – December 31
History of Diving Museum Exhibit: Diving in Pop Culture
Visit the museum at 82990 Overseas Highway (mile marker 83) to see the latest exhibit with representations of diving in literature, advertising, film, television, games, music, attractions, collectibles, and more, while examining connections amongst these works. Museum staff has been collecting and researching all of the creative ways diving has been incorporated into pop culture for over 100 years.
OCTOBER
October 7 – October 9
Southernmost Marathon & Half / Key West Running Festival
Imagine running through the southernmost island in the United States while enjoying a break from the ordinary. The Southernmost Marathon & Half / Key West Running Festival promises just that- 26.2, 13.1 or 3.1 miles of ocean and gulf views, as well as iconic Key West landmarks. Join us this fall for Key West and the Florida Keys premier race – the Southernmost Marathon & Half. Come for the race and stay for a good time! All participants will receive an event t-shirt at packet pick up and finisher medal.
October 17
16th Annual “Tiger in the Woods” Golf Tournament
Registration begins at 7:00am, Tee-off at 7:30am @ Key West Golf Club
October 22 – October 23
Goombay 2021
We are very happy to let everyone know that Goombay 2021 has been approved.
Our festival dates are October 22 & 23
Let the party begin
October 22 – October 31
The 2021 Annual Fantasy Fest
The 2021 Annual Fantasy Fest is a 10-day celebration that is scheduled to take place October 22 to 31, 2021 in Key West, Florida. This iconic event started simply as a way to draw attention to the tiny island in the middle of October when tourism was notoriously slow. What started as a small parade grew into a massive event drawing nearly 75,000 people to Key West. Each year the theme changes, and this year it is “In Tune But Off Key.”Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!”
Apr 21 – Dec 31
History of Diving Museum Exhibit: Diving in Pop Culture
Visit the museum at 82990 Overseas Highway (mile marker 83) to see the latest exhibit with representations of diving in literature, advertising, film, television, games, music, attractions, collectibles, and more, while examining connections amongst these works. Museum staff has been collecting and researching all of the creative ways diving has been incorporated into pop culture for over 100 years.
NOVEMBER
November 5
Florida Keys SPCA 14th Annual Spring Social
Presented by Hank’s Hair of the Dog Saloon to benefit the homeless animals of the Lower Keys, join the FKSPCA’s biggest celebration of the year at the Key West Golf Course; includes dinner, a live & silent auction, entertainment, complimentary wine & beer with cash liquor bar. VIP tickets include a Champagne Reception starting at 5:30 p.m. before the main event, passed appetizers, a sneak peek at one of the largest silent auctions on the island, reserved seating and VIP food stations.
November 7 – November 14
Powerboat Races by Raceworld Offshore
Race World Offshore is excited to bring teams and fans to Key West for an amazing Offshore World Championship experience. Due to COVID-19, there will undoubtedly be some changes this year. However, RWO is the premier Offshore Racing Sanctioning body in the United States and our team is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event even with the mandatory guidelines that all will need to follow.
- Opening Ceremony in the Truman Waterfront Park
- Wednesday Race Truman Waterfront Cup and winners will be recognized with awards immediately after each race
- Friday Race Southernmost Continental Champion and winners will be recognized with awards immediately after each race
- Thursday & Saturday concert in Truman Waterfront Park (TBD)
- Friday Parade of boats on water with Florida Powerboat Club
- Online Registration for teams convenience
- 2nd Annual Build-A-Boat Contest
- Build-A-Boat to include USCG, Fire, Police, Community & Race Teams
- Online hospitality ticket sales for convenience
- Water shuttle on race day for Outer Mole VIP guests – Easy walk from Duval (to be confirmed)
- Sunday UIM World Champion Awards & Closing Ceremonies in TWP Amphitheater immediately following final Sunday race
- Awards Ceremony to include public
November 17 – November 21
Key West Film Festival
The Key West Film Festival – where passion meets paradise – is an annual celebration of contemporary cinema in a historically rich, artistically vibrant, and culturally diverse island community.
KWFF strives to showcase the best of Florida filmmaking talent, while highlighting visiting filmmakers and industry leaders through discussions and workshops, with access to some of the biggest names in the film business. The festival also looks to support the next generation of local student filmmakers with scholarships and other key awards.
DECEMBER
December 2
8th Annual POSH – Paws Often Seal Hearts (A fund raising event for the Florida Keys SPCA)
WHEN: Thursday, December 2nd, 2021 – 6:30 pm – 9:30pm
New Orleans 2nd Line Parade begins at 9:30 pm with after party at Green Parrot
WHERE: Audubon House & Tropical Gardens at 205 Whitehead Street
WHY: Benefiting our local SPCA to help prevent cruelty to animals & find families for our homeless animals.
ENTERTAINMENT: Live from New Orleans, The Yat Pack! (A band that brings back the days of Dean Martin, Frank Sinatra, Louie Prima, Bobby Darin and New Orleans Jazz with an awesome horn and rhythm section)
THEME: POSH will be Key West formal attire for the evening event featuring the ‘Fascinator Hat’ – A fascinator is a headpiece, a style of millinery. It is usually a large head decoration on a band or clip with elaborate trimmings and decoration like a formal hat and it can incorporate a base to make a miniature hat. Everyone is welcome to wear one.
December 4
City of Key West Holiday Parade 7pm – 8:45pm
A Key West holiday favorite for young and old alike. The parade begins at Bayview Park on the corner of Eisenhower, Leon and Truman Avenues.
December 11
Eighth Annual Florida Keys SPCA Parade of Paws
Join the Florida Keys SPCA at the Higgs Beach Dog Park from 10 a.m. – 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2021 Royal Court. Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach! Costumes encouraged! All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.
And a little taste of 2022 for you.
January 15, 2022
FLORIDA KEYS SEAFOOD FESTIVAL
The Seafood Festival celebrates our community by bringing families and friends together in a joyful and fun environment to sample the local catch. This family-friendly event was created to showcase local seafood and the Keys’ commercial fishing industry by providing the freshest seafood.
I’m seeing the dates of the 15th and 16th. Will update as we know more. But ya got lots of time before this comes around.
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Please be aware that because of COVID-19, pools, beaches, popular attractions, restaurants, bars, grocery, and specialty retail may or may not be open during this time. Including community pools in the Truman Annex, The Colony, Duval Square, Key West Golf Course, La Brisa, 1800 Atlantic, and Winward Park. Also included are Smathers Beach, Higgs Beach, and the beach at Fort Zachary Taylor State Park. Should such places currently be open in Key West, Florida, please note that they could close at any time without warning. Events may also be cancelled by the Event Coordinator or Promoter. Please check their websites for the latest information.